


Fear of Falling

by JulzSnape



Category: Supernatural
Genre: Angst, Dating, Dean is Bad at Feelings, Destiel Forever Fic Challenge, Emotional Hurt/Comfort, Fake/Pretend Relationship, Fallen Angels, Falling In Love, First Dates, Fluff, Fluff and Angst, Friends to Lovers, Human Castiel, Hurt Castiel, Impala Makeouts, M/M, Meteor, Prompt 35, Prompt Fic, Sam Is a Good Friend, Stars, Unconventional date
Language: English
Status: Completed
Published: 2015-06-28
Updated: 2015-06-28
Packaged: 2018-04-06 18:21:59
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 9,162
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4232043
Author URL: https://archiveofourown.org/users/JulzSnape/pseuds/JulzSnape
Summary: <blockquote class="userstuff">
              <p>“How does dating work?” Castiel asked as he dried a bowl thoughtfully. There was a pregnant pause as Dean stopped washing the frying pan and just stared at Castiel with a bemused look. </p><p>“Er, I’m not sure I’m the best person to go to for dating advice, buddy. Not really the dating type, if you know what I mean.”</p><p>Castiel cocked his head to the side in a familiar, autonomic gesture he’d never outgrown. “I don’t think I know what you mean.”</p><p>Dean sighed as he turned off the water and dried his hands on a dish towel, turning his back towards the sink and leaning back against the countertop. The front of this plain white shirt had gotten a little wet from the dish water splashing up, and a hint of pinkish skin could be seen through the thin material. Castiel snapped his eyes back up to Dean’s face, hoping his cheeks didn’t do that blushing thing and give away his distracted wandering eyes.</p>
            </blockquote>





	Fear of Falling

**Author's Note:**

  * For [msarahv](https://archiveofourown.org/users/msarahv/gifts).



> Destiel Forever Fanfic Challenge
> 
> Prompt # 35:
> 
> Cas is human now after falling. He wants to experience & learn all there is about being human. He wants to start dating but is worried because he doesn’t know what to do or how to act on a date. Dean comes up with a plan for him to take Cas out on his first “date” to give him some tips on how to have a successful one. Dean finds himself melting at all the cute ways Cas is behaving on the date & realises he wishes the date was for real.

It had been a rough few months for Castiel after the fall. After being turned away from the bunker by a desperate and panicking Dean, living on the streets, and almost being murdered by the Reaper he lost his virginity to, Castiel had not been eager to re-join the dating scene. However, he found himself watching what Dean grumpily called ‘chick flicks’ (yet he still watched them) and feeling a certain yearning he couldn’t really identify.

After watching A Walk to Remember and crying his eyes out, clutching a throw pillow to his chest as he curled up on the couch, Castiel finally realized he was lonely. Of course he had Sam and Dean around, and he loved them, but it wasn’t the same. He craved the companionship and love of a significant other. He knew the only way he would find that was to start dating, but no matter how many chick flicks he watched, Castiel had no idea how to date.

It was a quiet night in the bunker, just after dinner. Sam had cleared the dishes away and Dean had volunteered to wash them, since Sam had cooked. Castiel offered to dry the dishes, since last time he had washed them he’d broken three plates and plunged his hands into the water, catching a steak knife to his palm. He’d been relegated to drying duty ever since.

“Dean, can I ask you a personal question?” the former angel asked as he accepted the plate Dean handed to him, wiping it down before setting it aside on the pile of stacked plates on the counter.

Dean shrugged and gave Castiel a searching look. “Yeah, sure; I think we’ve known each other long enough that personal questions are kind of open season, ya’ know?”

Castiel smiled at the hunter, feeling warmth wash over him. Dean had been so supportive and helpful to him after he lost his grace and had to learn how to function as a human. It had taken him a little while to trust Dean again after he had been kicked out of the bunker, but he understood that Dean needed to do whatever he could to save his brother.

“How does dating work?” Castiel asked as he dried a bowl thoughtfully. There was a pregnant pause as Dean stopped washing the frying pan and just stared at Castiel with a bemused look.

“Er, I’m not sure I’m the best person to go to for dating advice, buddy. Not really the dating type, if you know what I mean.”

Castiel cocked his head to the side in a familiar, autonomic gesture he’d never outgrown. “I don’t think I know what you mean.”

Dean sighed as he turned off the water and dried his hands on a dish towel, turning his back towards the sink and leaning back against the countertop. The front of this plain white shirt had gotten a little wet from the dish water splashing up, and a hint of pinkish skin could be seen through the thin material. Castiel snapped his eyes back up to Dean’s face, hoping his cheeks didn’t do that blushing thing and give away his distracted wandering eyes.

“Well, I’ve never really successfully done the dating thing, Cas. I mean the only two girls I ever really considered to be girlfriends were Cassie and Lisa. Neither of those ended well.”

“But you still dated them, so you know how it works,” Castiel insisted. He had mimicked Dean’s position across from the hunter, leaning back against the center island in the kitchen. Dean looked relaxed, physically, but Castiel could see in his eyes that he wasn’t comfortable with this conversation. He knew Dean avoided talking about Lisa and Ben at all costs because it was just too painful.

“Where’s this coming from, Cas? Got a girl you’ve got your eye on?” Dean asked with a chuckle, clearly trying to change the subject and focus back to Castiel. Dean had side-stepped towards the fridge and grabbed a beer, then held one out questioningly to Castiel, who nodded, only because he needed something to do with his nervous hands.

Castiel accepted the beer bottle from Dean after the lid had been popped off for him – he still couldn’t figure out the bottle opener without tearing the little metal cap apart with his failed attempts to pry it from the lip of the glass. He took a small drink, feeling the bubbles scatter across his tongue and the tang of alcohol stung as it went down. He’d never get used to these human senses.

“No, no girls. I just…I think I’m lonely, Dean. I see those couples in the movies and TV shows and I feel this longing. It’s something I don’t think I ever really felt as an angel. Angels are lone beings; we… _they_ …don’t require companionship, and angels are not bred like humans. I want to feel what Rose and Jack felt. I want to love someone like Chandler loved Monica. Is that abnormal for a human?”

Dean seemed to be studying Castiel carefully as he drank from his own beer. There was a certain sadness and understanding in the man’s eyes, as if he knew exactly what Castiel meant, but didn’t want to say as much.

“It’s not abnormal to want to share your life with someone. But like I said, I’m not the best example of how to have a healthy relationship…of any sort. Especially being a hunter, Cas; there’s not much opportunity for white picket fences when you’re in this line of work. If you want to date, I say go for it.”

“But I don’t even know where to start. Who do I ask? _How_ do I ask? What do I wear, where do I take a date?”

“Woah, woah! Ok, I get it…you need help with the basics. Well, the first step is to find someone to ask. Are you sure you don’t have your eye on anyone? No one at the supermarket or anything?”

“Dean, I’ve barely left the bunker. There are only three people I think I’ve ever had…feelings for, now that I know what those emotions truly feel like. As an angel, even when I did feel that way towards someone, it was dampened,” Castiel explained as he took another deep drink of his beer. He felt antsy; maybe asking Dean had been a bad idea. He could try asking Sam, maybe.

Dean cocked an eyebrow at Castiel before slugging back half his beer in one gulp. “Three people? Ok…well, what did you like about these people? Maybe…maybe you could start with one of those people?” Dean asked tentatively, a confused look on his face. It was obvious he was curious who those three people were, but he was keeping himself from asking. If Cas wanted him to know, he’d have told him. Plain and simple.

Castiel frowned as he shook his head with a deep sigh. “That’s not possible. One is…dead, another wasn’t interested, and the third…well, I don’t think that would go over very well.”

“How do you know that? Maybe you just need to ask. Lesson one of dating: you have to have the balls to actually ask the girl out. Most girls who are interested in actually dating and not just hooking up aren’t going to be the one to make the first move. If they do, they’re probably not thinking long term.”

Castiel huffed as he finished his beer and set the bottle down a little roughly on the counter behind him, turning back to Dean with an exasperated look. “You’re assuming I only meant women, Dean. What if it’s a man? Who makes the first move then?”

Dean nearly spit his mouth full of beer all over his best friend, but managed to choke it down instead, which went down the wrong pipe and triggered a small coughing fit. As he got his breath back and wiped his watering eyes, Dean gave Castiel an almost panicked look.

“Damn it, Cas, I was not expecting that! I’m _really_ not the one to ask about that. I guess I did just assume, so…sorry, I never thought that you were into… _that_ ,” Dean finished awkwardly as he rubbed the back of his neck and looked anywhere but directly at the former angel.

Knowing he had made Dean extremely uncomfortable now, Castiel decided this had definitely been a bad idea. “You know what, never mind. I’ll figure it out eventually. Thanks for trying, Dean. I’m going to head to bed.”

Castiel was halfway to the kitchen door before Dean’s voice stopped him. “Wait! Cas…wait. Look, I’m sorry. I didn’t mean to make it weird, and I do want to help you. I just kind of suck at this whole talking shit out thing. I’m not good at explaining things so…so what if I showed you instead?”

Castiel’s head did that turn to the side once more, which he noticed almost always brought a little smile to Dean’s lips. “Show me? I don’t understand.”

Dean took a deep breath and wiped his palms on his thighs, finally pinning Castiel with an intense look. “I can’t teach you how to date from making a graph or some shit like that, but I can give you a practical lesson. I’ll take you out on a mock date, show you what I do, and you can take it from there. Would that work?”

Castiel was stunned into speechlessness until Dean’s tentative expression began to turn to panic. “I…Yes, that would work. But Dean, are you ok with doing something like that?”

A smirk spread out on Dean’s face as he shrugged. “Well, it won’t be for real, and you’re my best friend, Cas. I know this human crap isn’t easy for you, and I want to help. So, yeah – I’m ok with doing something like that. Tomorrow night, I’ll pick you up at seven.”

Castiel’s brow scrunched together as he gave the hunter a bemused look. “Dean, we live together.”

“I know, but if this is supposed to be like a real date, I’m gonna do it right. So, I’ll pick you up in the Impala at seven. Be ready by the door; I’ll knock and everything.”

Castiel wasn’t quite sure Dean was completely serious, but decided to go along with it. “Ok…seven it is. See you…well I’ll see you at breakfast won’t I?”

Dean chuckled and shook his head. “Nah, we’re gonna do this right, build up the anticipation. Oh, and wear something kind of nice. Not your suit and tie, but kind of dressy. You’ll figure something out. Goodnight, Cas.”

Castiel was still standing in the kitchen even after Dean had gripped his shoulder briefly and left, presumably to head to bed himself. He could feel his stomach start to do weird things, like there was a wind storm in his gut. _I’m going on a date tomorrow._

Dean _is taking me on a date tomorrow!_

A startling thought finally gripped Castiel as he realized what he was feeling was nervousness and excitement. “What do I wear?!”

*D*C*

_What the hell did I just agree to?_

In the heat of the moment, it had seemed like the most logical, best idea. Dean sucked at talking about feelings and he was not a good teacher at all. But Dean was pretty good at showing someone how to do something – he was a hands on learner and teacher, so to speak.

But taking Cas on a date? Where the hell had that come from? Of course he wanted to help his best friend out, but he wasn’t sure this was such a good idea after all. Dean never did anything by half, so if he did this, he was going all out. He was going to make sure he took Cas on the perfect date. The guy deserved a chance to learn before being thrown to the wolves of the dating world. No woman (or man, _holy shit_ ) would really believe Cas has never dated before, seeing as he appeared to be in his late thirties or early forties in Jimmy’s body.

So yeah, maybe Dean had jumped the gun a little bit and committed to something before really thinking about it, but that seemed to be an integral part of Dean’s personality; act first, think later. He was determined to give Cas the best date ever, though, because Dean had been on too many bad first dates and didn’t want his best friend to learn the hard way.

*C*D*

Dean made sure he was up early to snag some breakfast and head out to start setting everything up. He knew Cas wouldn’t be up until a little later, preferring to sleep in now that he actually had to sleep.

Sam was of course up earlier than Dean, sitting at the kitchen table with a cup of coffee, an everything bagel, and an old beat up book.

“Woah – you’re up early. Did you even sleep?” Sam asked as he marked his page in his book and set it aside on the table.

Dean rolled his eyes and grabbed a coffee cup from the cupboard. He filled it with the remainder of the fragrant pot Sam had brewed, taking a deep breath of the rich coffee smell. “Yeah, I slept. I’ve got some errands to run in town, so I thought I’d get an early start. You haven’t seen Cas, right?”

Sam scoffed before taking a large bit of his bagel and waving it at Dean. “Cas up before ten in the morning? Only if the Bunker caught fire. What do you have to do in town? I might need a few things from – ”

“No! Uhh…I mean, I’ve got some, er, personal things to do,” Dean blurted, feeling his cheeks heat up in a blush that went straight up to his ears. Yeah, that wasn’t going to make Sam suspicious at all.

Sam’s expression turned from bemused to his classic Bitch Face. “Dean, please tell me you’re not going out to get laid. We have more important things to focus on right now, you know, and I think you’re being a little selfish. Sometimes you just gotta handle it yourself like a normal guy does – ”

“Sam – SAM! Dude, stop! I do not want to hear about you ‘handling yourself’ ok? I’m not going out to get laid, jack ass. I just have some stuff to do, stuff for Cas, ok?” Dean tried to explain, feeling the blush get worse as it traveled down his neck to his chest. This had turned out harder than he thought. Why couldn’t Sam just believe he was going to run normal, everyday errands? Stupid nosey brother and his poking and prodding.

“Well if you’re getting stuff for Cas, why can’t you pick me up a few things too? Geez, Dean, it’s not like I’m asking you to drive to the other side of the country or something. I just need some toiletries and stuff. If it’s that much of a hassle, I’ll go with and you can just drop me off at the store while you go do…whatever.”

Dean rubbed a hand over his tired eyes as he slunk down into the kitchen chair across from his brother. “Look…Ok, hear me out, alright? I’m actually, er…I’m going on a date, so I’m going to make reservations and get an outfit, maybe clean the Impala up a little bit.”

Sam’s Bitch Face melted into a grin as he drained the last of his coffee and set his cup aside. “A date? Dean, have you _ever_ been on an actual date? And who on earth could you have met recently? Not that I’m not happy for you! I am, really.”

Dean scowled as he drained his own coffee cup and stood up to rummage around in the fridge for something to eat. He grabbed a slice of left over pizza and took a bite, still cold. Sam gave him a disgusted look, which just made Dean smirk around his half chewed pizza, disgusting his little brother further.

“Of course I’ve been on a real date, jerk. It’s not…not what you think. It’s not some random chick I met at the store or something. Uhh, also, Cas and I won’t be eating here tonight, so don’t bother making dinner.”

Dean could tell he had confused Sam with that comment, his brother’s face falling into a confused moue. He could tell the exact moment Sammy finally got it as his eyebrows flew into his hair and his jaw dropped.

“Wha – Cas? Really? _Finally!_ ”

“Woah, hey – don’t go planning a wedding or anything, Sammy. It’s just a mock date, ya know, not for real,” Dean quickly corrected, a little surprised by Sam’s excited reaction. He thought his brother might be a little confused and maybe awkwardly accepting, but practically writing their vows? What the hell?

Sam’s enthusiastic expression crumbled as he pinned Dean with a suspicious look. “A ‘mock date’? You’re going into town to make reservations and clean the Impala up and _buy new clothes_ , but it’s not a real date? Yeah, sure Dean.”

“No really! Cas asked me how dating works and you know I suck at explaining shit, so I decided to just show him instead. It’s not real; it doesn’t mean anything,” Dean said with a nonchalant shrug as he stuff the crust of his slice of pizza into his mouth. He really needed to get going, before Cas woke up.

“I don’t think this is a good idea, Dean. You’re going to give Cas the wrong impression.”

“Nah, he knows it’s not real. We’ve already talked about it; don’t worry. Just, you know…if he needs a little bit of help, be there for him? I’m not going to be around to help him, and I know he’s probably going to need help picking out clothes and stuff. Semi-casual, no monkey suits or anything like that. And help him with his hair; this new Dad Hair thing he has going on is…ugh, no. I gotta go, the restaurant opens in an hour and I want to make sure it’s not booked up.”

“Wait, Dean! Just – please don’t mess this up, ok? You’ve got Cas in a very delicate position. Don’t hurt him,” Sam pleaded with an anxious look towards his older brother.

Dean made a face and scoffed. Leave it to Sammy to be over cautious about a _fake date_. “How could I mess up a fake date or hurt Cas? It’ll be fine. Make sure he’s ready by seven!”

Sam sighed gustily, his expression one Dean knew well; the ‘I know something you don’t know’ look that Dean hated. “I’m sure you could find many ways to mess this up.”

“Shut up, asshat.”

“Jerk.”

“Bitch.” Dean chuckled as Sam threw a waded up napkin at his head as he beat a quick exit out of the kitchen. He had work to do.

*D*C*

Sitting on his bed, staring dumbly at his dresser that contained very few clothes, Castiel felt a surge of panic hit him in the chest. Dean had said to dress nice, but not in his whole suit. Did that mean he should wear part of his suit? What else did he really have that would considered ‘nice’?

Castiel stood and pulled open his top left drawer which contained his shirts. He riffled through them, trying to figure out if any of them were nice enough. There were mostly plaid flannels, a couple of Dean’s worn out band t-shirts Castiel had borrowed (indefinitely), and a couple of henleys. Just as Castiel was about to start pulling every article of clothing he owned out, there was a gentle knock on his door.

“Come in,” said Castiel, sure that it was Sam and not Dean. Dean had left very early that morning, Sam had said, though he wouldn’t tell him what he was up to.

Sam’s large frame entered the room, a sheepish expression on his face as he rubbed his palms together in a classic nervous gesture for the Winchesters. “Hey, Cas. Uh…need any help?” Sam asked, clearly trying to be nonchalant but looking as though he was about to squirm out of his clothes completely.

Castiel sighed and dropped his arms, which held two shirts he had been comparing. “Please? I have no idea what I’m doing. Not only do I not know how to prepare for a date, but I’m not exactly an expert on human fashion. Dean said to dress nice, but to not wear my suit. I’m not sure he understands the limitations of my wardrobe choices.”

A gentle smile spread across the younger Winchester’s face as he finally seemed to relax. He moved further into the room and held out his hands for the shirts Castiel had been comparing. “Well, you can make pretty simple clothes look dressy if you pair them right. First things first: no flannel. I know that’s like ninety-five percent of our wardrobes, and while flannel can be dressed up too, let’s stay away from it this time. And I swear if Dean wears a flannel I’ll punch him for you and make him go change.”

“That’s not necessary; I don’t think wearing flannel on a date warrants a punch, Sam,” Castiel assured the hunter. Sometimes it was very hard for him to tell when Sam and Dean were joking. He sensed this was one of those times, but he wanted to be sure Sam didn’t punch Dean for something like wearing flannel.

Sam chuckled and set aside the flannel the angel had handed him, moving towards the dresser drawers to see what they had to work with. After pulling out a few shirts, Sam finally held up a black sweater that Dean had given him. It was light and had a V-neck, and it had hardly been worn by Dean, so it was almost like new.

“This sweater is simple enough but what you wear with it is what will make the difference. What are our pant options?” Sam asked as he carefully folded the sweater and placed it aside on Castiel’s bed.

Castiel pulled open the bottom two drawers and stepped back to allow Sam to look through them for suitable options. There were old jeans Dean had outgrown, some sweat pants Sam had given him, and his suit pants. Castiel had not been exaggerating when he said there weren’t many options.

“Ok, so…not much here. Hold on, I’ll be right back,” Sam said as he quickly left the room, leaving Castiel to look down at his open drawers with a confused expression.

Castiel was grateful for Sam’s help, but felt as though he would never get the hang of this kind of stuff. How was he supposed to know the rule about no flannel on dates? Who made these rules, and where could he find them? Just as Castiel was contemplating researching in the library, Sam came back into the room with a pair of dark gunmetal gray jeans.

“Dean hates these jeans because he says they’re too form fitting; he prefers loose clothing. They might be a bit big in the waist on you, but use can use your belt from Jimmy’s suit if you need to. Here, put these and the sweater on, and I’m going to look for some shoes for you. I don’t think your dress shoes or the Chucks Dean bought you would match very well. Be right back,” Sam said for the second time in just a few minutes as he thrust the pair of jeans into the angel’s hands and closed the door behind him.

Castiel held out the jeans and then held them up to his hips. They looked like they would fit him, but he also had no idea what size pants he was supposed to wear. Dean had tried to explain the length and width measurements when he took him clothes shopping the first time, but Castiel had opted for more sweatpants instead, which came in simple sizes like small, medium, and large.

Shucking his current pair of sweatpants and the AC-DC shirt Dean had given him, Castiel pulled on the jeans and the black sweater Sam had helped him pick out. The jeans were pretty form fitting, tighter in the thighs and seat of the pants than Castiel was used to. After buttoning and zipping the jeans up they were a tiny bit loose and hanging off his hips just a little, but not really enough to warrant a belt. The length was a bit long on him, however, as Dean was taller than him and always bought longer length pants than he had said Castiel would need.

There was a quick knock on the door, startling Castiel out of his musings about pant lengths. “You decent? I think I found some boots that might fit you.”

“Uh…yes, I’m decent,” Castiel answered, not quite sure what Sam was actually asking, but seeing no reason not to let him back into the room, either.

The younger Winchester stopped as he walked into the room, a pair of black leather boots hanging from one hand, and stared at Castiel. “Wow, see what I mean? Simple sweater and add some nice tight jeans, and you look like a million bucks. Good thing I found you some boots, though; those jeans are a bit long on you. The boots might be a size too big, but Dean taught me this trick growing up when we had to share shoes and my feet weren’t quite as big as his. Just wear two pairs of socks and they’ll fit decently enough,” Sam said as he handed the boots to Castiel and then rummaged in the dresser for a few pairs of socks to hand over.

Castiel sat down on the edge of his bed and pulled the two pairs of socks on, then slipped the boots on, which zipped up on the sides and had a slight heel. When he stood up, the hem of his jeans no longer touched the floor, thanks to the heel. He stretched his arms out and gave Sam a questioning look, feeling completely out of his depth.

“Well, do I look nice enough for wherever Dean is taking me?”

Sam smiled and nodded as he reached over to brush some lint from the Castiel’s shoulder. “I’m not really sure where he’s taking you because he refused to tell me, but I think you look great. Now let’s do something with that hair of yours.”

Castiel gave Sam a confused look before following the hunter out of his room and towards the bathroom down the hall. “What do you mean? What’s wrong with my hair?”

“Nothings ‘wrong’ with it necessarily, but I just think you should style it a little bit,” Sam explained as he opened the cabinet under the sink in the bathroom and pulled out a few small bottles that Dean liked to call ‘Sammy’s beauty products’.

“So you probably don’t want to overdo it, just give it a little character,” Sam said as he pulled out a small, round jar and twisted the lid off. “This is pomade. I get the stuff that’s more like a cream than the greasy classic pomades so your hair won’t come out all stiff and slick.”

Sam swiped his fingers in the jar, collecting a small glob of the cream/grease, whatever it was, and then rubbed it between his palms. He stood behind Castiel, who was facing the mirror, and then he was running his hands and fingers through Castiel’s hair, tousling it almost artfully. After he was done tweaking a few pieces of hair here and there, he stood back and admired his work, smiling proudly as he wiped his hands on a small towel.

Castiel was still looking in the mirror at his hair. It didn’t look all that different, but instead of it being swept to one side, it looked like it had just been blown around by the wind, but it a purposeful way.

“Do you think I should shave? Do dates require no stubble?” Castiel asked as he turned away from the mirror and met Sam’s eyes. Castiel hated shaving and had had more than a few accidents in the past, which was why he usually had a good few days of stubble. The less he had to shave, the better. Sam chuckled and shook his head.

“Nah, it’s not required. I know some women who prefer smooth skin, and some who prefer stubble. It’s all about preference. As for men I’m not really sure, but I don’t think Dean really minds your stubble, considering his own. Besides, that usually only really matters if there’s going to be kissing involved, so…” Sam trailed off, rubbing the back of his neck as if he realized he had stumbled onto a tricky subject.

“Will there be kissing involved? Do dates usually involve kissing?” Castiel asked, as they left the bathroom and headed towards the War Room. Castiel had kissed only a few times before, and only ever women. Before he could really think about anything else, an image popped into his mind of Dean pulling him close and kissing him gently, their stubble rubbing together pleasantly. He was torn out of his daydream by Sam’s nervous laugh.

“Uh, well, sometimes they do. Usually first dates end with a simple goodnight kiss, but it really depends on how the date goes. I uh…I’m not sure what Dean’s plan is on that subject. I’ll leave that up to him. Anyways, I think you’re all set and ready. It’s about a quarter to seven so Dean should be here soon.”

“I still think it was unnecessary for Dean to pick me up like this. It would be just as simple to get ready and leave together,” Castiel said as he sat at one of the table with Sam, who had opened his laptop to do some research.

“He wanted it to feel like a real date and pick you up. I think Dean has something great planned. I hope you guys have fun. Even if it’s, you know…not real or whatever,” said Sam with a vague hand gesture. He stared at his monitor as if avoiding Castiel’s eyes.

“You know, this was all Dean’s idea. I had just asked him for advice on how dating works and this was his plan. Do you think this was a mistake?”

Sam’s attention was once again all on Castiel as he pushed his laptop aside and fixed the former angel with a piercing look that made Castiel nervous. Was Sam bothered by Dean taking him on a mock date because he didn’t like seeing Dean with another man? Castiel didn’t think Sam had a discriminatory bone in his body, but maybe he had misjudged.

“I don’t really know, honestly. As far as I know, Dean is going to consider this a completely platonic favor for his best friend, but he’s going to go all out and make sure you feel like this is a real date, because Dean doesn’t half-ass anything. You understand that, right?”

Castiel wasn’t sure what he was supposed to say. He knew that’s what he had agreed to, but there was a small part of him that wanted to believe this was real, that didn’t want to acknowledge that Dean was only doing him a favor.

Ever since Castiel had pulled Dean from Hell, everything had changed. He used to think he knew exactly what he was doing, leading his own garrison of angels, following what he thought were his father’s wishes. He had held on to the hope that his father was still out there, still calling the shots and would be there when they truly needed him, but he was gone. Castiel’s faith in his father had died, and his faith was put into man instead – the Righteous Man, specifically.

He had given up everything he knew and loved and trusted, all for Dean. If he had to go back and do it all again, he wouldn’t change anything, because everything they had been through led to this moment. Sure, Castiel was still adjusting to falling and becoming human, but even through all of the struggles, Dean had always been there for him. They had a couple of bumps in the road, but all that mattered was that he was here now, with Dean and Sam, and he knew he could count on the Winchesters.

Now that he had a full range of human emotions, Castiel knew that the way he felt about Dean was incredibly different to how he felt about Sam, or anyone else really. He knew what love was, knew what it felt like, and though he was scared to acknowledge or admit it, he was sure that he had been in love with Dean for years, but never really knew what that meant until he fell.

Besides, Dean had said that he wasn’t attracted to men, so that had to mean he didn’t feel that way about Castiel. This was just a friendly favor, Dean was just helping Castiel out in his time of need. He wouldn’t allow himself to overthink what it meant when his stomach churned and his heart clenched every time he reminded himself _this isn’t real, this isn’t real…_

Before Castiel could respond, there was a loud knocking on the door at the top of the stairs leading down into the War Room of the bunker. He jumped up, feeling every cell of his body quake with nerves.

“That must be your date, Cas. Go answer the door,” said Sam, a big goofy, knowing smile on his face as he nodded towards the door.

Castiel didn’t say anything, just gave a jerky nod as he convinced his legs to star moving towards the stairs, then up them, then to the door. He took a deep breath, looked down at Sam one last time (who gave him a thumbs up), and opened the door.

*D*C*

Dean pulled up to the bunker, his Baby shining and gleaming in the fading sunlight after her wash and wax. He’d had the Impala detailed, inside and out (though he strictly denied any access to the trunk whatsoever). As he cut the engine, Dean sat gripping the steering wheel, feeling that increasing _‘what the fuck am I doing?’_ sensation settle in his chest.

He had spent all day planning the perfect first date for Cas, and while he was excited to get to help his friend out, he was worried about how Cas might feel, how _he_ might feel. This was a mock date, and he was determined to make sure Cas had a great time and got the full experience, but what if he didn’t understand that this wasn’t real? What if…what if Dean _liked_ it?

Before he could settle into full panic, Dean got out of the car and grabbed something off of the seat beside him before walking to the front door of the bunker. He felt stupid knocking on the bunker door instead of just going in, but he had told Cas he would pick him up, just like a real date, and he was determined to stick to it. He almost held his breath as he waited for the door to open, which felt like years. Finally the door opened with a creak (Dean needed to oil the hinges), and Castiel was there in front of him, smiling nervously.

Dean was shocked speechless for a moment as he took in Cas’ outfit. The man seemed to be wearing all articles of clothing that at one point or another had belonged to Dean, but somehow Castiel made them look far better than Dean ever had. The black sweater clung to his chest and the dark jeans hung off his hips and extended down to a pair of boots Dean had bought on impulse and worn once. The former angel’s hair was tussled stylishly, but not overdone. Seeing the man in his own clothing always did weird thing to Dean’s gut, but this was entirely different. He was afraid to acknowledge the heat that had grown low in his stomach, and what it actually meant.

“Cas, you look amazing,” Dean finally said after realizing he had been checking his date out for a little too long. Good thing Castiel had no idea he’d made a faux pas already.

Castiel’s eyes began to trail up and down Dean’s body, and the hunter blushed as he realized he was being checked out in kind. He supposed that made sense, as he knew Castiel was trying to follow his lead and was returning the favor.

“You look very good as well, Dean,” Castiel said as his own cheeks blushed a little, his gaze moving so that his eyes did not directly meet Dean’s as he bit his lip nervously. It was…adorable.

“This is for you,” Dean said as he held out the single blue rose to the former angel, whose eyes grew wide as he reached out instinctively and took it. His eyes finally met Dean’s as a slow smile spread across his face.

“I’ve never seen a blue rose before, it’s beautiful.”

“It reminded me of your eyes,” Dean said, delivering the classic line he had used on a few dates in the past. This time, he actually meant it, and not as a foot in the door to getting into Castiel’s pants. Dean pushed that thought aside quickly.

Castiel’s entire expression softened as he held the rose close to his chest and then held out his hand, clearly waiting for Dean to take it and walk him to the car. Maybe Castiel was going to be better at this dating thing than he had originally let on. Dean took his hand and paused to let Cas close the bunker door before leading him to the Impala. He opened the passenger door and let the former angel climb in before shutting it and jogging around to his side and getting in.

“So, where are we going on this date?” Castiel asked with a bright smile as he absentmindedly stroked the petals of his rose in the passenger seat.

Dean chuckled as he started the Impala, putting it into drive before flashing a smirk at his date. “Dinner first. The rest is a surprise.”

“Tease,” Cas said as they pulled away from the bunker, startling a bark of laughter out of Dean as he headed towards the restaurant he had made reservations at.

*C*D*

They were halfway through their meal when Dean realized he was smiling like an idiot at the story Cas was telling him about the first time he had ever used a toaster and how he’d nearly pulled the gun Dean had given him and shot it. He was smiling and laughing as he ate his salmon, and Dean couldn’t think of a time he had seen Cas this happy before.

“It was all for naught, anyways, since my toast was completely burnt to a crisp. So I had no breakfast and had a small heart attack because of the toaster. I think that was the morning you taught me how to make scrambled eggs. I never mentioned the failed toast.”

Dean laughed as he cut up his steak. “Thank you for not shooting the toaster, Cas. The bullet probably would have ricochet all over the kitchen and hit you or something.”

Cas chuckled and rolled his eyes, smiling at Dean as he lifted his wine glass. “It would be my luck to end up with a gunshot while trying to make toast. This wine is very sweet, isn’t it?”

“Yeah, it’s a Moscato. I thought we’d start with one of the lighter wines to ease you into wine before going with the rich reds. It’s an acquired taste,” Dean explained, sipping at his own glass of chilled Moscato. It was a very simple wine, but it tasted great and he knew Castiel loved sweets.

Castiel’s head turned to the side in that gesture Dean had come to love so much as he fixed Dean with a curious look. “I had no idea you knew so much about wines, Dean. I don’t think I’ve ever seen you drink wine before.”

Dean realized his mistake too late as he struggled to find some lie, any lie, to tell instead of the truth. The longer he stalled, the more confused Castiel looked, so he gave up. He had intended to avoid all talk of exes, as that was a huge faux pas on a first date. But this was also Cas, and Cas would understand, right?

“Oh, uh…Lisa was really into wine and kind of got me into it for a while. I haven’t really drank much wine since…well, in a while.”

Castiel’s hand was suddenly on top of Dean’s, giving it brief squeeze before simply resting on top. “I understand, Dean. You don’t have to talk about it. Now, what’s for dessert?” the former angel asked with a smile which seemed to ignite something in Dean’s chest. He was starting to feel like the tables had turned a little bit, and Cas was taking the lead somehow.

Dean signaled the waiter and asked for the check instead, which caused the most adorable pout to form on Castiel’s face. “I have different plans for dessert. You’ll see.”

“You mean the date isn’t over?” Castiel asked as his expression brightened and he squeezed Dean’s hand once more.

Dean chuckled and before he could think about it, he turn his hand over and gripped Castiel’s fingers in his own, his thumb rubbing across the back of his friend’s knuckles instinctively. “Of course it isn’t, Cas. We eat together for almost every meal; that’s not a date.”

The waiter had come back with Dean’s change, and had taken off with their plates. Dean left the change as the waiter’s tip and stood up, holding his hand out to Cas once more. “Come on, onto surprise number one.”

Castiel took his hand and smiled as they made their way out of the restaurant together, his eyes bright with excitement at the mention of surprises. “There’s more than one surprise?”

Dean couldn’t help but smile like an idiot as they got in the Impala and headed towards the small ice cream shop he had come across when shopping for clothes earlier in the day. At the shop, Dean whispered to the girl behind the counter, who smiled beatifically at him and Cas as she began scooping ice cream into two cones.

“Don’t I get to choose my own flavor, Dean?” Castiel asked with a frown as he accepted the cone the girl held out to him and inspected the ice cream suspiciously.

“It’s part of the surprise. Try it, you’ll like it,” Dean explained as he took a lick of his own cone and waited for Cas to try it himself. He watched as Cas tentatively took a small lick of ice cream, then closed his eyes and gave a small moan of pleasure.

“Honey, it tastes like honey!” Castiel said as he licked at his cone more enthusiastically.

Dean felt his cheeks heat up and looked away from Cas’ pink tongue swiping at his ice cream, feeling that heat in the pit of his stomach grow. What was happening to him? Cas’ moan and his enthusiastic ice cream eating was doing very strange things to Dean’s gut and thoughts. Perhaps ice cream hadn’t been the best idea.

“It’s made from real honey comb. I thought you’d like it. Come on, we can eat these one the way to your next surprise,” Dean said as he led the way out of the ice cream shop.

Castiel had instinctively reached for Dean’s hand, their fingers threaded together as they walked down the sidewalk towards where the Impala was parked. Dean felt slightly panicky at the thought of someone seeing them holding hands, but then brushed it away. Anyone who saw them and didn’t like it could fuck off; they had no right to judge them. Dean would hold whoever’s hand he damned well pleased.

“I find I really like surprises, Dean,” said Castiel as he continued to lick at his ice cream cone while walking down the street hand in hand with his date.

Dean felt pleasure zing up his spine as he saw how happy Cas looked and sounded. Maybe he wasn’t half bad at this dating thing either. “Most people like surprises, Cas. I’m glad you’re one of them. Just don’t get the Impala’s handle sticky, please.”

Castiel gave Dean an almost offended look as they separated at the car and got in on their respective sides. “I wouldn’t dream of getting ice cream on your Baby. I have more respect for her than that.”

Laughing, Dean pulled the Impala away from the curb and towards his next and final surprise. So far the date was going really well and it seemed like Cas was having a good time. He really hoped Cas liked his next surprise. As he was driving, Dean started thinking about all of the other dates he had been on before. Most of them didn’t really count, as he had really only taken the girl out to eat somewhere before taking her back to a motel for a night of fun and never spoke to them again. This was different, though. Dean really wanted Castiel to enjoy himself and have a good time, and there was no ulterior motive. He just wanted his friend to be happy after everything the fallen angel had been through.

He watched Castiel from the corner of his eye as he drove and finally let himself just feel. He was glad to see Castiel happy for once. He had felt terrible kicking Cas out of the bunker after he first fell, but he was so scared for Sammy that he did everything he could to make sure he was ok. He felt like an even bigger dick after everything that happened with Gadreel. He was surprised that Cas had forgiven him and agreed to come back to the bunker.

He had been trying to make it up to his friend ever since, which was part of the reason Dean had decided to take Cas on this date. Not only did he want to help Cas out, but he wanted to treat Cas to a nice meal and do something spontaneous with him, to show him that he meant so much more to Dean than he had ever allowed himself to really admit to Cas before.

He watched as Castiel fought to keep his ice cream in the cone as it began to melt and then figure out what to do with the melted ice cream he had caught with his palm to prevent it from getting on the car. After a few glance around for inspiration, Cas began to just lick the ice cream from his palm and fingers with a shrug.

Dean quickly pulled his eyes back to the road, lest he drive completely off it while watching Castiel’s tongue. He felt the heat in is stomach roar into a full blown fire, and that was something else he wasn’t quite ready to acknowledge just yet either.

After driving for about fifteen minutes, Cas began to squirm in his seat and peer out the windows, as if looking for some kind of clue as to where they were going. Dean found the dirt road he was looking for and pulled off the main road, going slow since his Baby was pretty low to the ground and wasn’t exactly made for all terrain trips. He drove a little ways down the road, then cut the engine and turned off the headlights. It was almost pitch black except for a little sliver of moon in the night sky.

“We’re here,” Dean said as he got out of the car and then went around the car to open the passenger door for Cas.

Castiel looked extremely confused as he climbed out of the car and looked around the desolate little road they had ended up on, then met Dean’s eyes with a question in his own shockingly blue eyes.

“Dean, what are we doing out here?”

Dean just smiled and lifted himself onto the hood of the Impala, then held out his hand to Cas so he could help his friend up beside him. Once Cas was sitting beside him on the hood, looking even more confused and almost concerned now, Dean wrapped an arm around his shoulders and leaned back until they were both laying against the windshield and across the hood of his Baby. “Watch.”

Castiel shifted until he was cradled in Dean’s embrace a little better, then followed Dean’s advice and looked up into the dark night sky. Their eyes had adjusted to the darkness now, and what looked like hundreds, maybe even thousands of stars twinkled down at them. Dean heard Cas gasp softly beside him.

“So many stars…It’s beautiful,” Castiel whispered as he moved closed to Dean and laid his head gently against the hunter’s shoulder.

“Keep watching.” Dean squeezed his arm around Cas, feeling the fire in the pit of his stomach cool to a low simmer, and a surge of butterflies start up instead. It was like he was a teenage girl with a crush, for God’s sake.

He suddenly felt all of the air leave his lungs as he realized what he was actually feeling. This _was_ a crush, and he could finally admit to himself that he wanted this to be a real date. Dean felt his heart clench at the missed opportunity; they were having their first date, but it wasn’t even real.

Before Dean could think to bring this up to Cas, the man beside him gasped even louder and pointed suddenly towards the sky above them, drawing Dean’s attention to the stars above instead. “Look! Dean, the stars…they’re falling.”

Dean watched as a few shooting stars went whizzing across the sky and smiled. “It’s a meteor shower, Cas. It’s called the Perseids. Tonight is one of the peak nights for the shower and the phase of the moon is perfect because the less light, the easier it is to see the meteors. I’ve seen them a few times before on the road with Dad and Sammy, but I’ve never had the chance to come out and actually watch them. It’s pretty awesome, right?”

Silence met Dean’s words, and suddenly Dean felt himself seize with panic. Had he done something wrong? Had this been a bad idea? Just then, he heard a soft sniffle and labored breathing and tore his gaze from the sky to stare at Castiel’s tear streaked face instead. He was crying while clutching Dean’s jacket to his chest.

“Cas? Are you ok?”

“Yes, I’m fine. It’s just…it reminds me of the fall, of seeing all of my brothers and sisters falling to earth and not being able to do anything to stop it. I was such an idiot, Dean. I fell for Metatron’s trick and now all of the angels are on earth, confused and probably hurt.”

Dean felt his stomach tighten and suddenly realized his great date idea had just made him the biggest dick on the planet. How could he forget about the fall as the angels were cast out of Heaven by Metatron’s spell? How could he forget how terrible Cas had felt, _still_ felt?

“Fuck, Cas, I’m sorry. I’m an idiot, this was a bad idea. We should go home,” Dean said as he began to sit up. He was stopped by Cas clinging to his jacket and pulling him back down to the hood.

“No, it’s ok. I think it’s beautiful. I thought it looked beautiful during the fall too, but I couldn’t appreciate the beauty then. I’m glad you brought me out here, Dean. Now I know there is beauty like these meteors that don’t come with pain as well,” Castiel said as he turned to look at Dean instead of the sky.

Dean was speechless. Cas had caught him completely off guard and he still felt like a giant jack ass for bringing Cas out here and thought maybe they should just leave anyways because he had upset his date, which was just his damn luck. His panicked thoughts came to a screeching halt as Dean felt a pair of soft, warm lips press against his own.

He lay motionless for what felt like forever as he tried to process the fact that Cas was actually kissing him. The pressure was gentle, almost tentative, and the sensation of feeling Cas’ five o’clock shadow scratch against his own was new, but definitely not unpleasant. Dean felt Cas’ hand unclench from his jacket and instead brush against his cheek before settling on his neck, and it was as though the former angel’s touch had awoken him and opened the flood gates.

Dean began to kiss Castiel back in earnest, angling his head to make the kiss deeper and pull Cas closer against him. At some point Cas had turned over onto his side, and with another shift, Dean was now underneath him. The weight on top of him was pleasant and welcome, and Dean felt no shame in lifting his hands and burying them in Castiel’s tousled hair and pulling his head closer to deepen the kiss even more.

A moan rent the air as Castiel pulled away and nipped at his bottom lip, and suddenly the kiss was no longer tentative or unsure. Dean’s tongue slid languidly against Castiel’s as he invited the man’s tongue into his own mouth. They kissed deeply and passionately, with a lot of tongue and stubble burn that was sure to be irritating later but didn’t bother either of them in the slightest bit just then.

Castiel pulled away hesitantly as he panted to catch his breath. He blue gaze bore down into Dean’s eyes, as the fire that had started in the pit of his stomach had set a blaze through his entire body and along every nerve ending.

“Dean…Can this be a real date now?”

“I think it’s been a real date the entire time, we just didn’t know it until now.”

Castiel laughed softly, a smile lighting up his face as he leaned down and pressed another kiss to Dean’s pliant lips.

“Good. I get to plan our second date.”

Dean smiled against Castiel’s lips and wrapped his arms around him, holding him close as they lay against the hood of his Baby, the meteor shower forgotten above them as they were consumed in a different kind of fall entirely.

“Deal.”

**Author's Note:**

> Thanks for reading, and I hope you liked it, Msarahv! This one gave me a lot of trouble and I fought with it for a long time, but in the end I'm pretty happy with how it came out. Please let me know what you think!


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